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Compositions comprising 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate and 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol

a technology of cyclohexaminopropenyl methylcyclohexaminopropenyl methylcyclohexaminopropenyl methylcyclohexaminopropenyl methylcyclohexaminopropenyl methylbenzene, which is applied in the directions of organic chemistry, plant/algae/fungi/lichens ingredients, etc., can solve the problem that the thermostable emul

Active Publication Date: 2020-04-07
NATURAL EXTRACTION SYST LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0011]In some embodiments, a composition comprises one or more of sodium ion (Na+), potassium ion (K+), calcium ion (Ca2+), magnesium ion (Mg2+), chloride ion (Cl−), sulfate (SO42−), bicarbonate (HCO3−), and carbonate (CO32−).
[0012]In some embodiments, a composit

Problems solved by technology

Thermostable emulsions of cannabidiol frequently display unfavorable characteristics including undesirable taste.

Method used

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  • Compositions comprising 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate and 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
  • Compositions comprising 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate and 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
  • Compositions comprising 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate and 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol

Examples

Experimental program
Comparison scheme
Effect test

example 1

on of 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate

[0041]0.5 grams of 1R,6R CBD was dissolved in 3.3 milliliters 0.5 molar potassium hydroxide (0.5 M KOH) in ethanol to produce 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate. The conversion of 1R,6R CBD to 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate was readily confirmed by color because 1R,6R CBD has a yellow-brown color and 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate has a deep purple color.

[0042]The 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate was diluted with 26.7 milliliters of 0.1 molar sodium carbonate (0.1 M Na2CO3) and divided into three aliquots of 10 milliliters each, each aliquot containing approximately:[0043]167 milligrams 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate[0044]21 milligrams potassium ion[0045]41 m...

example 2

on of Salts Comprising 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate

[0049]A first aliquot from Example 1 was lyophilized to produce salts including a potassium 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate salt and a sodium 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate salt.

example 3

uting 1R,6R CBD

[0050]0.1 milliliters of 5 molar citric acid (5 M citric acid) was added to a second aliquot from Example 1 to reconstitute 1R,6R CBD from 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate. The reconstitution of 1R,6R CBD was confirmed by color.

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Abstract

Various aspects of the disclosure relate to compositions comprising 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate and 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol.

Description

PRIORITY CLAIM[0001]This patent document claims priority to U.S. Provisional Patent Application No. 62 / 780,169, filed Dec. 14, 2018, and U.S. Provisional Patent Application No. 62 / 787,717, filed Jan. 2, 2019, each of which is incorporated by reference in its entirety.BACKGROUND[0002]The Cannabis plant produces cannabidiolic acid, which displays only nominal pharmacological activity. Cannabidiolic acid can be converted into cannabidiol, which displays robust pharmacological activity, by heating cannabidiolic acid under vacuum.[0003]Cannabidiol is sparingly soluble in water. Attempts have been made to improve the solubility of cannabidiol to produce beverages suitable for human consumption, for example, by emulsification. Thermostable emulsions of cannabidiol frequently display unfavorable characteristics including undesirable taste. Improved methods of solubilizing cannabidiol are desirable to produce beverages comprising cannabidiol.BRIEF DESCRIPTION[0004]Various aspects of the disc...

Claims

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Application Information

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IPC IPC(8): A23L33/105C07C39/19A23L29/00A23L2/52A61K36/185
CPCA23L33/105A23L2/52A61K36/185A23L29/035A23V2002/00A23V2250/2132
Inventor METCALF, DOUGLAS G.
Owner NATURAL EXTRACTION SYST LLC